Andrew Rossi’s new doc is an all-access pass to Anna Wintour’s annual Met Gala that may tip the scales in fashion’s favor.

It’s practically unheard of that when Anna Wintour calls you to do something, you don’t comply.

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But for documentary filmmaker Andrew Rossi’s latest film The First Monday in May, it wasn’t just about having the opportunity to work with the inimitable editor-in-chief of Vogue magazine, it was more about his predilection for unpacking premiere institutions–in this case, the Metropolitan Museum of Art and Wintour’s annual fashion bonanza the Met Gala.

Like his previous films including Page One: Inside the New York Times and Le Cirque: A Table in Heaven, Rossi explores why certain entities hold sway in their respective fields–in the process, amplifying the heartbeat behind their monolithic success. And with The First Monday in May, focusing on last year’s theme and exhibition China: Through the Looking Glass, Rossi is granted rare, behind-the-scenes access to the making of what’s been accurately described as the Super Bowl of fashion, all through the meticulous guidance of Wintour and the Met’s curator in charge of the Costume Institute, Andrew Bolton.

There’s more at play, however, than documenting the who’s who of A-listers decked out in couture costumes. What Rossi aims to contribute to is the ongoing debate of whether or not fashion is art.

“The jury is still out as to whether fashion can really be a fine art and deserves to be within the Metropolitan Museum,” Rossi says. “So looking at [Bolton’s] process and walking through the museum over his shoulder, we get to appreciate what the Met does in a new way–that both challenges our preconceptions about the institution but also reinforces some of those standards of excellence.”

One of the most salient explanations made in the doc as to why the art world tends to snub fashion is that fashion is still considered to be in the “female” space, regardless of the fact that many of the top designers are men, therefore it’s seen as “less than.” That misogynistic residue from centuries of subjugation is slowly being scrubbed away by curators like Bolton who, in 2011, had a major turning point in his battle to validate fashion in the Met’s hallowed halls with exhibition Savage Beauty, a retrospective of the late, luminary Alexander McQueen, which drew more than 650,000 visitors in its three-month run.

“[Museums face] so much competition that renders the analog experience more and more of in danger of becoming extinct,” Rossi says. “So you have in Andrew Bolton a visionary curator who’s able to convene an audience around a theme, whether it be Alexander McQueen’s work or a bigger, abstract concept like the transmission of Chinese culture through many different forms. And he does it in a way that’s academically rigorous but also emotional–and on some levels commercially savvy. That’s something that I think is a disruptive force in the legacy of museums.”

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That same caliber of savviness can also be said of Wintour, who, over the years, has transformed the Met Gala from an intimate gathering of fashion elite to the celebrity-drenched fundraising blitz of today, quite literally by hand.

Rossi captures just how meticulously hands-on Wintour is with her legendary soiree, moving chairs and tables to her specifications, overseeing seating arrangements, etc. What’s missing, though, is the frigid air of condescendence or haughty belittlement that’s dogged Wintour for nearly her entire career (see, The Devil Wears Prada).

“I’ve always been fascinated to make movies that go behind the scenes of institutions. But beyond that, I wanted to unpack the mythology surrounding Anna Wintour who’s kind of a pop culture institute herself,” Rossi says. “There’s certain expectations for the audience. There’s a sense that here’s a movie about Anna Wintour and they want to see some of the cliches reinforced about her. I’m not interested in perpetuating cliches, so we have to look at her role in a critical way.”

Part of Wintour’s role with the Met Gala has been to set art, fashion, and celebrity on a collision course–and there are those times when the crash is so complete, it’s felt well beyond any of those institutions. Rihanna’s show-stopping Guo Pei designed gown stormed the Internet last year, reaching people who may not have given the Met Gala a second thought let alone heard of it. It’s a moment Rossi plays up to fever pitch of romance in The First Monday in May, with Nat King Cole crooning “Stardust” as Rihanna makes her slow-mo entrance to the blinding lights of photographers.

“Her wearing that dress in that moment and its ability to virally explode on the Internet, the dress sort of takes her over in a way that is bigger than if it was on a mannequin or if somebody who wasn’t the famous Rihanna that we know,” Rossi says. “That to me is the culmination of the whole argument–that Anna understood the fusion of celebrity and fashion together transcend what they each are individually.”